Naftifine

Naftifine
Names
Trade namesNaftin,[1] Exoderil, others
IUPAC name
  • (2E)-N-methyl-N-(1-naphthylmethyl)-3-phenylprop-2-en-1-amine
Clinical data
Drug classAntifungal
Main usesAthlete's foot, joke itch, ring worm[2]
Side effectsIrritation, redness, itching, burning, allergic reaction[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
External links
AHFS/Drugs.comMonograph
MedlinePlusa688020
Chemical and physical data
FormulaC21H21N
Molar mass287.406 g·mol−1

Naftifine sold under the brand name Naftin among others, is an antifungal medication used to treat athlete's foot, joke itch, and ring worm.[2] While it has some benefit against candidiasis other medications are better.[2] It is applied to the skin as a cream or gel.[2]

Side effects occur in less than 5% of people.[1] These may include irritation, redness, itching, burning, and allergic reaction.[1] There is no evidence of harm in pregnancy, though such use is not well studied.[3] It is similar to terbinafine and is believed to work by blocking sterol biosynthesis.[4][2]

Naftifine was approved for medical use in the United States in 1988.[2] In the United States a 45 gram tube costs about 85 USD as of 2021.[5] It is not available in the United Kingdom.[4]

Mechanism of action

Its precise mechanism of action is unknown, but may involve selectively blocking sterol biosynthesis via inhibition of the squalene 2,3-epoxidase enzyme.[6][7] It is also an anti-inflammatory.[2]

Chemistry

The half-life is approximately 2–3 days.[7] The metabolites are excreted in the urine and feces.[8]

References

  1. 1 2 3 4 Gupta, Aditya K.; Mays, Rachel R.; Folley, Kelly A. (2019). "42. Topical antifungal agents". In Wolverton, Stephen E.; Wu, Jashin J. (eds.). Comprehensive Dermatologic Drug Therapy (4th ed.). Elsevier. p. 486. ISBN 978-0-323-61211-1. Archived from the original on 2021-10-09. Retrieved 2021-10-07.
  2. 1 2 3 4 5 6 7 "Naftifine Monograph for Professionals". Drugs.com. Archived from the original on 19 July 2021. Retrieved 11 November 2021.
  3. ↑ "Naftifine topical Use During Pregnancy". Drugs.com. Archived from the original on 23 November 2020. Retrieved 11 November 2021.
  4. 1 2 Ritter, James M.; Flower, Rod; Henderson, Graeme; Loke, Yoon Kong; Rang, Humphrey P. (2020). "54. Antifungal drugs". Rang & Dale's Pharmacology. Elsevier. pp. 690–695. ISBN 978-0-7020-7448-6. Archived from the original on 2021-08-28. Retrieved 2021-10-07.
  5. ↑ "Naftifine Prices, Coupons & Savings Tips". GoodRx. Retrieved 11 November 2021.
  6. ↑ Robertson Dirk B, Maibach Howard I, "Chapter 61. Dermatologic Pharmacology" (Chapter). Bertram G. Katzung, Susan B. Masters, Anthony J. Trevor: Basic & Clinical Pharmacology, 11e: http://www.accesspharmacy.com/content.aspx?aID=4517257 Archived 2012-03-03 at the Wayback Machine.
  7. 1 2 Micromedex DRUGDEX Drug Point: Naftifine Hydrochloride. Accessed at www.thomsonhc.com/../BeginWith#secN10184 Archived 2019-12-17 at the Wayback Machine, February 18, 2010.
  8. ↑ AccessPharmacy: Drug Monographs: Naftifine. Accessed at http://www.accesspharmacy.com/drugContentPopup.aspx?mid=6620&section=10 Archived 2012-03-03 at the Wayback Machine, February 18, 2010.
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